Cheapest return MDW–SJU flights, December

AirHint found the following cheapest return flights from Chicago (MDW) to San Juan (SJU) in December 2026 (see full year).

Return flights

01 Dec - 12 Dec Southwest Airlines
11 Dec - 21 Dec Southwest Airlines
14 Dec - 19 Dec Southwest Airlines
05 Dec - 14 Dec Delta
23 Dec - 30 Dec Southwest Airlines
22 Dec - 30 Dec Southwest Airlines
30 Dec - 03 Jan Southwest Airlines
21 Dec - 01 Jan Southwest Airlines
20 Dec - 04 Jan Southwest Airlines
27 Dec - 02 Jan Delta
27 Dec - 01 Jan Southwest Airlines

Also check the deals for one-way flights from Chicago to San Juan in December.

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The deals are updated regularly. The prices may go up as tickets are purchased by other travellers. Only the cheapest flights are offered. Select a price to book and secure these cheap prices.

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